Diisopropylamine → HCID 21964651, compound

HRID 2212395Notes

Reaction equation

HRID 2212395 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.[CH:13]1[C:23]2[CH:22]=[CH:21][C:20]3[CH:24]=[CH:25][CH:26]=[CH:27][C:19]=3[CH:18]([C:28]#[N:29])[C:17]=2[CH:16]=[CH:15][CH:14]=1.Br[CH2:31][CH2:32][CH2:33][C:34]#[N:35]>C1COCC1>[C:34]([CH2:33][CH2:32][CH2:31][C:18]1([C:28]#[N:29])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:23]=2[CH:22]=[CH:21][C:20]2[CH:24]=[CH:25][CH:26]=[CH:27][C:19]1=2)#[N:35]

Participants

6

Reactant 4

HCID 7912DiisopropylamineHCID 214124-BromobutyronitrileHCID 14950891HCID 14950891, compoundHCID 178418339Butyllithium

Product 1

HCID 21964651HCID 21964651, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-5 °C

Procedure

To a −5° C. solution of diisopropylamine (0.143 ml, 1 mmol) in THF (1 ml) was added dropwise nBuLi (0.67 ml, 1.06 mmol, 1.6 M in hexane). After 20 minutes stirring at −5° C., a solution of 5H-dibenzo[a,d]cycloheptene-5-carbonitrile (prepared according to: Regnier G. J. et al. J. Med. Chem. 1992, 35, 2481–2496) (0.2 g, 0.9 mmol) in THF (1 ml) was added dropwise. After 15 minutes at −5° C., a solution of 4-bromobutyronitrile (0.1 ml, 1 mmol) in THF (1 ml) was added slowly. The reaction mixture was allowed to warm up slowly to room temperature, stirred overnight and quenched with water and ether. Aqueous phase was extracted with ether and the combined organic phases were washed with water, dried with Na2SO4 and concentrated in vacuo. The residue was chromatographed over silica gel (hexane-ethylacetate 9:1) to provide 5-(3-cyano-propyl)-5H-dibenzo(a,d]cycloheptene-5-carbonitrile (0.2 g, 76%) as a colorless oil, MS: m/e=284 (M+).

Workup

  1. waitAfter 15 minutes at −5° C.
  2. temperatureto warm up slowly to room temperature
  3. stirringstirred overnight
  4. customquenched with water and ether
  5. extractionAqueous phase was extracted with ether
  6. washthe combined organic phases were washed with water
  7. dry with materialdried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed over silica gel (hexane-ethylacetate 9:1)

Sources & evidence

ORD record
ord-7fcebad5c20d4442ac88c088f20fde7a
Source dataset
uspto-grants-2006_09
Patent number
US07101917B2

Reaction notes

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